CN111116427A - Preparation method of fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether - Google Patents
Preparation method of fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether Download PDFInfo
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- CN111116427A CN111116427A CN201911390992.2A CN201911390992A CN111116427A CN 111116427 A CN111116427 A CN 111116427A CN 201911390992 A CN201911390992 A CN 201911390992A CN 111116427 A CN111116427 A CN 111116427A
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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Abstract
The invention discloses a preparation method of fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether, which comprises the following steps: reacting chloral, tetrafluorosultone and N, N-dimethyl tetrafluoroethylamine in a first solvent under the action of a catalyst, and washing, layering and rectifying after the reaction is finished to obtain fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether; (2) reacting fluorosulfonyl tetrafluoroethyl (trichloro-trifluoroethyl) ether with metal fluoride in a second solvent, and after the reaction is finished, washing, layering and rectifying to obtain fluorosulfonyl tetrafluoroethyl (monochloro trifluoroethyl) ether; (3) reacting the fluorosulfonyl tetrafluoroethyl (chlorotrifluoroethyl) ether with alkali, and after the reaction is finished, layering and rectifying to obtain the target product fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether. The invention has the advantages of mild reaction conditions, easily obtained raw materials, simple process and contribution to industrial production.
Description
Technical Field
The invention relates to the fields of electrolytic cells, hydrogen fuel cells and the like, in particular to a preparation method of fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether.
Background
The fluorosulfonyl tetrafluoroethyl (trifluorovinyl) ether is one of the important raw materials for synthesizing short-side-chain perfluorosulfonic acid ion exchange membranes.
The perfluorinated sulfonic acid ion exchange membrane has the advantages of strong chemical stability, high mechanical strength, high conductivity under high humidity, large current density under low temperature, small proton conduction resistance and the like, and is an electrolytic cell
One of the key components of a hydrogen fuel cell. The short-side-chain perfluorosulfonic acid ion exchange membrane can keep the water content in the membrane due to higher content of sulfonate groups, and the single cell output performance under low humidity is more excellent than that of a long-side chain, so that higher battery performance is maintained.
CF2＝CFOCF2CF2SO2The preparation method of F mainly comprises the following steps:
(1) epihalohydrin process:
the Asahi glass-seed patent JP2009167120A uses pentafluoro-3-bromo-1, 2-epoxypropane as raw material, and CF is generated by addition and decarboxylation2＝CFOCF2CF2SO2F。
The Dajin patent JP2010235568A uses 1, 3-dichloro-1, 2,3, 3-tetrafluoro propylene oxide as raw material, and CF is generated by addition and decarboxylation2＝CFOCF2CF2SO2F。
The Dajin patent WO2010114144A1 takes 1,1, 3-trichloro-2, 3, 3-trifluoro epoxypropane as raw material, and CF is obtained by addition and decarboxylation2＝CFOCF2CF2SO2F。
Dupont patents US3301893 and US3560568 report processes for the addition of tetrafluorosultones to hexafluoropropylene oxide.
(2) Great gold patent CN101052616A reports CF2＝CFOCF2CF2SO2Fluorination of Cl with potassium fluoride to obtain CF2＝CFOCF2CF2SO2And F, processing.
(3) Dupont patent US6388139 reports that CF2ClCFClOCF2CF2SO2F is dechlorinated in the presence of zinc powder to obtain CF2＝CFOCF2CF2SO2And F, processing.
(4) CN101696178B patent of Katsumadai Kabushiki Kaisha Co., Ltd reports that trifluorovinyl sulfate and tetrafluorosultone react to generate in the presence of catalyst (cesium fluoride, potassium fluoride and hydrogen fluoride)CF2＝CFOCF2CF2SO2And F, processing.
By-products
These synthetic processes have some disadvantages, or the processes are complicated, and raw materials are not easily available; or low efficiency, more waste gas, waste water and waste residues, and is not suitable for industrialization.
Disclosure of Invention
The invention aims to overcome the defects of the background technology and provides a preparation method of fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether, which has the advantages of mild reaction conditions, easily available raw materials, simple process and contribution to industrial production.
In order to achieve the purpose, the invention adopts the technical scheme that: a preparation method of fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether comprises the following steps:
(1) reacting chloral, tetrafluorosultone and N, N-dimethyl tetrafluoroethylamine in a first solvent under the action of a catalyst, and washing, layering and rectifying after the reaction is finished to obtain fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether;
(2) reacting the fluorosulfonyl tetrafluoroethyl (trichloro-monofluoroethyl) ether obtained in the step (1) with a metal fluoride in a second solvent, and after the reaction is finished, washing, layering and rectifying to obtain fluorosulfonyl tetrafluoroethyl (monochloro-trifluoroethyl) ether;
(3) reacting the fluorosulfonyl tetrafluoroethyl (chlorotrifluoroethyl) ether obtained in the step (2) with alkali, and after the reaction is finished, layering and rectifying to obtain the target product fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether.
As a preferred embodiment of the present invention, the first solvent in step (1) is at least one of N, N-dimethylformamide, N-dimethylacetamide and dimethylsulfoxide.
In a preferred embodiment of the present invention, the catalyst in step (1) is at least one of KF, CsF, and NaF.
As a preferred embodiment of the present invention, the second solvent in step (2) is at least one of acetonitrile, sulfolane and dimethyl sulfoxide, and the metal fluoride is at least one of KF, CsF and NaF.
In a preferred embodiment of the present invention, the base in step (3) is at least one of sodium hydroxide and potassium hydroxide.
As a preferred embodiment of the present invention, the molar ratio of chloral, tetrafluorosultone and N, N-dimethyltetrafluoroethylamine described in step (1) is 1: 1-2: 1-2, wherein the dosage of the catalyst is 5-15% of the mass of the chloral.
As a preferred embodiment of the invention, the temperature of the reaction in the step (1) is 20-50 ℃, and the reaction time is 2-4 h.
As a preferred embodiment of the present invention, the molar ratio of the fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether to the metal fluoride in the step (2) is 1: 2-4, wherein the dosage of the second solvent is 1-2 times of the mass of the fluorosulfonyl tetrafluoroethyl (trichloro fluoroethyl) ether.
In a preferred embodiment of the present invention, the temperature of the reaction in step (2) is 40 to 70 ℃, and the reaction time is 4 to 8 hours.
As a preferred embodiment of the present invention, the molar ratio of the fluorosulfonyltetrafluoroethyl (chlorotrifluoroethyl) ether to the base in the step (3) is 1: 2-4, wherein the reaction temperature is 50-70 ℃, and the reaction time is 5-8 h.
Compared with the prior art, the invention has the advantages that:
1. the method has the advantages that the method is simple in process flow and mild in reaction conditions, trichloroacetaldehyde and tetrafluorosultone are used as starting raw materials, an intermediate fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether is obtained in one step at low temperature through a high-activity fluorination reagent N, N-dimethyl tetrafluoroethylamine, and then fluoroolefin can be obtained through common means of fluorination, dehalogenation of hydrocarbon and the like, so that the preparation process is remarkably simplified;
2. the raw materials are easy to obtain, the cost is low, the used raw material chloral is a bulk chemical raw material, the tetrafluorosultone and the N, N-dimethyl tetrafluoroethylamine can be obtained by one-step reaction of tetrafluoroethylene, the raw materials are easy to obtain, the production cost is obviously reduced, and the industrial production is facilitated;
3. the yield is high, and the total reaction yield is over 72 percent and can reach 82.5 percent at most.
Detailed Description
The present invention will be described in further detail with reference to the following examples, but the present invention is not limited to the examples.
Example 1
1) A four-neck flask device with a reflux condenser tube (a tail end is provided with a drying tube) and a constant pressure dropping funnel is used for adding 75g of N, N-dimethylformamide, 1.5mol of N, N-dimethyl tetrafluoroethylamine, 14.8g of potassium fluoride and 147.5g (1mol) of chloral into a four-neck flask, stirring and mixing uniformly, controlling the reaction temperature to be 40 ℃, dropwise adding 1mol of tetrafluorosultone, reacting for 4 hours after the dropwise adding is finished, washing the reaction mixture with ice water, separating an organic layer, and rectifying to obtain 0.95mol of fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether. GC-MS qualitative and quantitative analysis shows that the product yield is 95%.
2) Using a four-neck flask device with a reflux condenser tube (a drying tube is arranged at the tail end), adding 132g of acetonitrile, 0.76mol of KF and 132g (0.38mol) of fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether obtained in the step 1) into the four-neck flask, stirring, heating, reacting for 4 hours at 60 ℃, and reacting
The mixture was washed with water, and the organic layer was separated and distilled to obtain 0.36mol of fluorosulfonyl tetrafluoroethyl (chlorotrifluoroethyl) ether. GC-MS qualitative and quantitative analysis shows that the product yield is 94.7%.
3) Adding 0.6mol of sodium hydroxide into a four-neck flask by using a four-neck flask device with a reflux condenser tube and a constant pressure dropping funnel to prepare a 10 wt% (wt%, mass percentage content) aqueous solution, uniformly stirring and mixing, controlling the reaction temperature to be 60 ℃, dropwise adding 95g (0.3mol) of the fluorosulfonyl tetrafluoroethyl (monochlorotrifluoroethyl) ether obtained in the step 2), reacting for 6 hours, separating an organic layer, and rectifying to obtain 0.27mol of the target product fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether. GC-MS qualitative and quantitative analysis shows that the product yield is 90 percent.
The total yield of the three steps is 81 percent.
Example 2
1) A four-neck flask device with a reflux condenser tube (a drying tube is arranged at the tail end) and a constant-pressure dropping funnel is used for adding 75g of N, N-dimethylacetamide, 1mol of N, N-dimethyltetrafluoroethylamine, 7.38g of cesium fluoride and 147.5g (1mol) of trichloroacetaldehyde into a four-neck flask, uniformly stirring and mixing, controlling the reaction temperature to be 20 ℃, dropwise adding 2mol of tetrafluorosultone, reacting for 2 hours after dropwise adding, washing the reaction mixture with ice water, separating an organic layer, and rectifying to obtain 0.96mol of fluorosulfonyl tetrafluoroethyl (trichloro-fluoroethyl) ether. And the GC-MS qualitative and quantitative analysis shows that the product yield is 96 percent.
2) Using a four-neck flask device with a reflux condenser tube (a drying tube is arranged at the tail end), adding 198g of sulfolane, 1.14mol of cesium fluoride and 132g (0.38mol) of fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether obtained in the step 1) into the four-neck flask, stirring, heating for reaction, controlling the reaction temperature at 70 ℃, reacting for 5 hours, washing the reaction mixture with water, separating an organic layer, rectifying to obtain fluorosulfonyl tetrafluoroethyl (monochlorotrifluoroethyl) ether
Base) ether 0.35 mol. GC-MS qualitative and quantitative analysis shows that the product yield is 92.1 percent.
3) Adding 0.6mol of potassium hydroxide into a four-neck flask by using a four-neck flask device with a reflux condenser tube and a constant pressure dropping funnel to prepare a 10 wt% aqueous solution, uniformly stirring and mixing, controlling the reaction temperature to be 60 ℃, dropwise adding 95g (0.3mol) of the fluorosulfonyl tetrafluoroethyl (chlorotrifluoroethyl) ether obtained in the step 2), reacting for 8 hours, separating an organic layer, and rectifying to obtain 0.28mol of the target product fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether. And the product yield is 93.3 percent by GC-MS qualitative and quantitative analysis.
The total yield of the three steps is 82.5 percent.
Example 3
1) Using a four-neck flask device with a reflux condenser tube (a drying tube is arranged at the tail end) and a constant pressure dropping funnel, adding 75g of dimethyl sulfoxide, 2mol of N, N-dimethyl tetrafluoroethylamine, 22.14g of sodium fluoride and 147.5g (1mol) of trichloroacetaldehyde into the four-neck flask, stirring and mixing uniformly, controlling the reaction temperature to be 40 ℃, dropwise adding 1.5mol of tetrafluorosultone, reacting for 4 hours after the dropwise adding is finished, washing the reaction mixture with ice water, separating an organic layer, rectifying,
fluorosulfonyltetrafluoroethyl (trichlorofluoroethyl) ether (0.9 mol) was obtained. GC-MS qualitative and quantitative analysis shows that the product yield is 90 percent.
2) Using a four-neck flask device with a reflux condenser tube (a drying tube is arranged at the tail end), adding 264g of dimethyl sulfoxide, 1.52mol of sodium fluoride and 132g (0.38mol) of the fluorosulfonyl tetrafluoroethyl (trichloro monofluoroethyl) ether obtained in the step 1) into the four-neck flask, stirring and heating for reaction, controlling the reaction temperature at 50 ℃, reacting for 4 hours, washing the reaction mixture with water, separating an organic layer, and rectifying to obtain 0.34mol of the fluorosulfonyl tetrafluoroethyl (monochlorotrifluoroethyl) ether. GC-MS qualitative and quantitative analysis shows that the product yield is 89.5 percent.
3) Adding potassium hydroxide 0.9mol into a four-neck flask to prepare 10 wt% aqueous solution by using a four-neck flask device with a reflux condenser tube and a constant pressure dropping funnel, stirring and mixing uniformly, controlling the reaction temperature at 60 ℃, and dropping
And separating an organic layer, and rectifying to obtain 0.27mol of the target product of the fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether. GC-MS qualitative and quantitative analysis shows that the product yield is 90 percent.
95g (0.3mol) of fluorosulfonyl tetrafluoroethyl (chlorotrifluoroethyl) ether obtained in the step 2) was added thereto, and the total yield in the reaction 7 was 72.5%.
Example 4
1) A four-neck flask device with a reflux condenser tube (a tail end is provided with a drying tube) and a constant-pressure dropping funnel is used for adding 75g of N, N-dimethylformamide, 1.5mol of N, N-dimethyl tetrafluoroethylamine, 14.8g of cesium fluoride and 147.5g (1mol) of chloral into a four-neck flask, stirring and mixing uniformly, controlling the reaction temperature to be 30 ℃, dropwise adding 1mol of tetrafluorosultone, reacting for 4 hours after the dropwise adding is finished, washing the reaction mixture with ice water, separating an organic layer, and rectifying to obtain 0.94mol of fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether. GC-MS qualitative and quantitative analysis shows that the product yield is 94%.
2) Using a four-neck flask device with a reflux condenser tube (a tail end is provided with a drying tube), adding 132g of acetonitrile, 1.52mol of KF and 132g (0.38mol) of fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether obtained in the step 1) into the four-neck flask, stirring and heating for reaction, controlling the reaction temperature at 70 ℃, reacting for 3 hours, washing the reaction mixture with water, separating an organic layer, and rectifying to obtain 0.37mol of fluorosulfonyl tetrafluoroethyl (monochlorotrifluoroethyl) ether. GC-MS qualitative and quantitative analysis shows that the product yield is 97.4%.
3) Adding 0.9mol of sodium hydroxide into a four-neck flask by using a four-neck flask device with a reflux condenser tube and a constant pressure dropping funnel to prepare a 10 wt% aqueous solution, uniformly stirring and mixing, controlling the reaction temperature to be 50 ℃, dropwise adding 95g (0.3mol) of the fluorosulfonyl tetrafluoroethyl (chlorotrifluoroethyl) ether obtained in the step 2), reacting for 8 hours, separating an organic layer, and rectifying to obtain 0.27mol of the target product fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether.
GC-MS qualitative and quantitative analysis shows that the product yield is 90 percent.
The total yield of the three steps is 82.4 percent.
Example 5
1) Using with reflux
A four-neck flask device with a condensing tube (a drying tube is arranged at the tail end) and a constant pressure dropping funnel, N is added into the four-neck flask,
75g of N-dimethylformamide, 2mol of N, N-dimethyl tetrafluoroethylamine, 22.14g of cesium fluoride and 147.5g (1mol) of trichloroacetaldehyde are uniformly stirred and mixed, the reaction temperature is controlled to be 40 ℃, 1.5mol of tetrafluorosultone is dropwise added, the reaction is carried out for 3 hours after the dropwise addition, the reaction mixture is washed by ice water, an organic layer is separated, and the organic layer is rectified to obtain 0.92mol of fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether. GC-MS qualitative and quantitative analysis shows that the product yield is 92 percent.
2) Adding into a four-neck flask by using a four-neck flask device with a reflux condenser tube (with a drying tube at the tail end)
Adding 198g of sulfolane, 1.52mol of KF and 132g (0.38mol) of fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether obtained in the step 1), stirring, heating for reaction, controlling the reaction temperature at 60 ℃, reacting for 3 hours, washing the reaction mixture with water, separating an organic layer, and rectifying to obtain 0.35mol of fluorosulfonyl tetrafluoroethyl (monochlorotrifluoroethyl) ether. GC-MS qualitative and quantitative analysis shows that the product yield is 92.1 percent.
3) Adding 1.2mol of sodium hydroxide into a four-neck flask by using a four-neck flask device with a reflux condenser tube and a constant pressure dropping funnel to prepare a 10 wt% aqueous solution, uniformly stirring and mixing, controlling the reaction temperature to be 70 ℃, dropwise adding 95g (0.3mol) of the fluorosulfonyl tetrafluoroethyl (chlorotrifluoroethyl) ether obtained in the step 2), reacting for 5 hours, separating an organic layer, and rectifying to obtain 0.26mol of the target product fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether. GC-MS qualitative and quantitative analysis shows that the product yield is 86.7 percent.
The total yield of the three steps is 73.5 percent.
Claims (10)
1. A preparation method of fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether is characterized by comprising the following steps:
(1) reacting chloral, tetrafluorosultone and N, N-dimethyl tetrafluoroethylamine in a first solvent under the action of a catalyst, and washing, layering and rectifying after the reaction is finished to obtain fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether;
(2) reacting the fluorosulfonyl tetrafluoroethyl (trichloro-monofluoroethyl) ether obtained in the step (1) with a metal fluoride in a second solvent, and after the reaction is finished, washing, layering and rectifying to obtain fluorosulfonyl tetrafluoroethyl (monochloro-trifluoroethyl) ether;
(3) reacting the fluorosulfonyl tetrafluoroethyl (chlorotrifluoroethyl) ether obtained in the step (2) with alkali, and after the reaction is finished, layering and rectifying to obtain the target product fluorosulfonyl tetrafluoroethyl (trifluoroethylene) ether.
2. The method according to claim 1, wherein the first solvent in step (1) is at least one of N, N-dimethylformamide, N-dimethylacetamide and dimethylsulfoxide.
3. The method according to claim 1, wherein the catalyst in step (1) is at least one of KF, CsF, and NaF.
4. The method according to claim 1, wherein the second solvent in step (2) is at least one of acetonitrile, sulfolane and dimethyl sulfoxide, and the metal fluoride is at least one of KF, CsF and NaF.
5. The method according to claim 1, wherein the base in step (3) is at least one of sodium hydroxide and potassium hydroxide.
6. The method for producing a fluoroolefin according to claim 1, wherein the molar ratio of chloral, tetrafluorosultone and N, N-dimethyltetrafluoroethylamine in the step (1) is 1: 1-2: 1-2, wherein the dosage of the catalyst is 5-15% of the mass of the chloral.
7. The method for preparing fluoroolefin according to claim 1, wherein the reaction temperature in the step (1) is 20 to 50 ℃ and the reaction time is 2 to 4 hours.
8. The process for producing a fluorine-containing olefin according to claim 1, wherein the molar ratio of the fluorosulfonyl tetrafluoroethyl (trichloromonofluoroethyl) ether to the metal fluoride in the step (2) is 1: 2-4, wherein the dosage of the second solvent is 1-2 times of the mass of the fluorosulfonyl tetrafluoroethyl (trichloro fluoroethyl) ether.
9. The method for preparing fluoroolefin according to claim 1, wherein the reaction temperature in the step (2) is 40 to 70 ℃ and the reaction time is 4 to 8 hours.
10. The process for producing a fluoroolefin according to claim 1, wherein the molar ratio of the fluorosulfonyltetrafluoroethyl (chlorotrifluoroethyl) ether to the base in the step (3) is 1: 2-4, wherein the reaction temperature is 50-70 ℃, and the reaction time is 5-8 h.
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| CN107286060A (en) * | 2017-06-22 | 2017-10-24 | 山东华夏神舟新材料有限公司 | End group is the preparation method of the perfluoroalkyl vinyl ether of sulfonyl fluoride group |
| CN110105252A (en) * | 2019-04-04 | 2019-08-09 | 浙江巨化技术中心有限公司 | A kind of preparation method of four fluoro ethyl of fluorosulfonyl (trifluoro vinyl) ether |
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- 2019-12-30 CN CN201911390992.2A patent/CN111116427B/en active Active
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| US3301893A (en) * | 1963-08-05 | 1967-01-31 | Du Pont | Fluorocarbon ethers containing sulfonyl groups |
| US6388139B1 (en) * | 1997-11-05 | 2002-05-14 | E. I. Du Pont De Nemours And Company | Production of perfluoro (alkyl vinyl) ethers |
| JP2010235568A (en) * | 2009-03-31 | 2010-10-21 | Daikin Ind Ltd | 1, 3-dichloro-1, 2, 3, 3-tetrafluoro propylene oxide, and method for producing the same |
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